NP-MRD: Showing NP-Card for (2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0255765)

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Record Information

Version

1.0

Created at

2022-09-07 20:21:52 UTC

Updated at

2022-09-07 20:21:52 UTC

NP-MRD ID

NP0255765

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

Description

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Based on a literature review very few articles have been published on (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222212D          

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M  END

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M  END


  Mrv1652309072222212D          

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    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  1  0  0  0
 19 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 17 35  1  0  0  0  0
 35 36  1  1  0  0  0
 15 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 13 40  1  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CO[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C[C@H](OC4=C3)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O14/c27-11-3-1-10(2-4-11)16-7-14(29)19-13(28)5-12(6-17(19)39-16)38-26-24(35)22(33)21(32)18(40-26)9-37-25-23(34)20(31)15(30)8-36-25/h1-6,15-16,18,20-28,30-35H,7-9H2/t15-,16-,18+,20-,21+,22-,23+,24+,25-,26+/m0/s1

> <INCHI_KEY>
RDZXIOLHICKFEI-HMLNJVQESA-N

> <FORMULA>
C26H30O14

> <MOLECULAR_WEIGHT>
566.512

> <EXACT_MASS>
566.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.415580342642386

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
-0.5734607466666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.529677646521824

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.579291799845732

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526580404084756

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
129.88500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      18.672   4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.672   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.004  -0.000   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    4   13                                                       
CONECT   13   12   14   40                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   35                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22   30                                                  
CONECT   30   29                                                            
CONECT   31   19   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   17   36                                                  
CONECT   36   35                                                            
CONECT   37   15   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   13    2                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₄

Average Mass

566.5120 Da

Monoisotopic Mass

566.16356 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@H]1CO[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C[C@H](OC4=C3)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H30O14/c27-11-3-1-10(2-4-11)16-7-14(29)19-13(28)5-12(6-17(19)39-16)38-26-24(35)22(33)21(32)18(40-26)9-37-25-23(34)20(31)15(30)8-36-25/h1-6,15-16,18,20-28,30-35H,7-9H2/t15-,16-,18+,20-,21+,22-,23+,24+,25-,26+/m0/s1

InChI Key

RDZXIOLHICKFEI-HMLNJVQESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Oxane
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162902657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0255765)

MOL for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0255765 ((2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)